GQ Rewinds: The Most Stylish Cars of the Past 50 Years

Developed to compete with Ford's Thunderbird, the Riviera—with its slick side-vents and its assertive front grill—offered the smoothest brand of masculinity going. It's still considered a design landmark, though we'll never understand how the makers of this car would one day dream up the Buick LaCrosse.

The SL stood for super leicht ("super light"), but these pert, tidy German roadsters exuded sturdiness beyond their size. The cars from this line, which was mostly unchanged through the '60s, were known as "pagodas" for their roofs, which were lower in the middle, and amounted to a key chapter in a long history of achingly sharp Benzes. The epitome of the good life—with a removable hard top.

Feeling a little more subdued after the exaggerated tail-fin and aerospace designs of the late-'50s, Cadillac tried its hand at understated elegance. The often overlooked '62 series (in one Mad Men episode, Don Draper buys the flashier Coupe de Ville) embraced a leaner, more linear aesthetic.

It debuted at the 1963 Frankfurt Auto Show as the 901, the first six-cylinder, road-ready Porsche ever build. With its iconic rear slope and unmistakable headlights, the 911 is one of the great cars designs of the century. No wonder they're still making them.

Named after Aston head David Brown, the DB5 was the first car with a film career, having appeared in Thunderball, Goldfinger, and many others. The DB was so hot that it came with a built-in fire extinguisher.

Only 350 of these lu roadsters ever made it out of the factory. Its vacation-in-Capri exterior belies the soul of a racing veteran. To give you some idea of its cachet, the one Steve McQueen owned went for $2.3 million at Christie's in '07.

Among the last generation of elegant Corvettes, the '63 Sting Ray, with its signature split rear window (later dropped for safety reasons), is its smartest, most distinctive vintage.

Photo: Courtesy of GM

Photo: Courtesy of GM

Buick Riviera (1964-65)

Developed to compete with Ford's Thunderbird, the Riviera—with its slick side-vents and its assertive front grill—offered the smoothest brand of masculinity going. It's still considered a design landmark, though we'll never understand how the makers of this car would one day dream up the Buick LaCrosse.

Photo: Courtesy of Mercedes

**Mercedes Benz 230, 250, and 280 SL (1960-63) **

The SL stood for super leicht ("super light"), but these pert, tidy German roadsters exuded sturdiness beyond their size. The cars from this line, which was mostly unchanged through the '60s, were known as "pagodas" for their roofs, which were lower in the middle, and amounted to a key chapter in a long history of achingly sharp Benzes. The epitome of the good life—with a removable hard top.

Photo: Courtesy of GM

**Cadillac Series 62 Eldorado (1962) **

Feeling a little more subdued after the exaggerated tail-fin and aerospace designs of the late-'50s, Cadillac tried its hand at understated elegance. The often overlooked '62 series (in one Mad Men episode, Don Draper buys the flashier Coupe de Ville) embraced a leaner, more linear aesthetic.

Photo: Courtesy of Ford

**Ford Mustang GT (1966-1968) **

Few cars better represent American cool than the Mustang, but the early Ponies still looked woefully timid compared to this fastback, which was immortalized in the Steve McQueen movie Bullitt.

Photo: Courtesy of Austin-Healy

Austin-Healey 3000 (1959-1967)

Though it debuted in 1959, the Austin-Healey 3000 (known as the "Big Healey") is too exquisite, too curvy, too unmistakably British not to include here. Who wouldn't look good driving one of these?

Photo: Courtesy of Porsche

Porsche 911 (1963-present)

It debuted at the 1963 Frankfurt Auto Show as the 901, the first six-cylinder, road-ready Porsche ever build. With its iconic rear slope and unmistakable headlights, the 911 is one of the great cars designs of the century. No wonder they're still making them.

Photo: Courtesy of Aston-Martin

Aston Martin DB5 (1963-65)

Named after Aston head David Brown, the DB5 was the first car with a film career, having appeared in Thunderball, Goldfinger, and many others. The DB was so hot that it came with a built-in fire extinguisher.

Photo: Courtesy of Jaguar

**Jaguar XKE (1969) **

Enzo Ferrari declared the E-type "the most beautiful car ever made." Who are we to quibble?

Photo: Courtesy of Ferrari

Ferrari 250 GT Berlinetta Lusso (1962-65)

Only 350 of these lu roadsters ever made it out of the factory. Its vacation-in-Capri exterior belies the soul of a racing veteran. To give you some idea of its cachet, the one Steve McQueen owned went for $2.3 million at Christie's in '07.

Photo: Courtesy of GM

Chevrolet Corvette Sting Ray (1963-67)

Among the last generation of elegant Corvettes, the '63 Sting Ray, with its signature split rear window (later dropped for safety reasons), is its smartest, most distinctive vintage.